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Hydrochloric Acid → N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amine

HRID 465968
Notes
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Reaction equation

HRID 465968 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.Cl.[N:12]1([NH:21][CH2:22][CH2:23][CH3:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C([O-])([O-])=O.[Na+].[Na+]>CN1CCCC1=O.O>[N:12]1([N:21]([CH2:22][CH2:23][CH3:24])[C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 53592776-ChloropurineHCID 107023901H-Indol-1-amine, N-propyl-

Product 1

HCID 178456864N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amineYield 25.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of 6-chloropurine (5.0 g, 0.032 mole) in 50 ml 1-methyl-2-pyrrolidinone, was added 1 ml ethereal-HCl; followed by a solution of N-(1H-indol-1-yl)-N-propylamine (5.2 g, 0.030 mole) in 50 ml 1-methyl-2-pyrrolidinone. After stirring at 120° C. for six hours, the mixture was cooled, poured into 500 ml water and stirred for five minutes, pH adjusted to 10 with Na2CO3 ; then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solution was evaporated to an oil, about 8 g, which was eluted on a silica gel column with ethyl acetate via high pressure liquid chromatography. The desired fractions were combined, then evaporated to yield 2.2 g (25%) of N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amine, m.p. 90°-5° C.

Workup

  1. temperaturethe mixture was cooled
  2. stirringstirred for five minutes
  3. extractionthen extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationAfter filtering
  7. customthe solution was evaporated to an oil, about 8 g, which
  8. washwas eluted on a silica gel column with ethyl acetate via high pressure liquid chromatography
  9. customevaporated

Sources & evidence

ORD record
ord-5e21a73129ce470a9cdb6208078de0f6
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05155098

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes